U.S. patent application number 15/562767 was filed with the patent office on 2018-03-22 for polymerizable composition for optical member, optical member, and spectacle lens base.
This patent application is currently assigned to HOYA LENS THAILAND LTD.. The applicant listed for this patent is HOYA LENS THAILAND LTD.. Invention is credited to Masahisa KOUSAKA, Tomofumi OHNISHI.
Application Number | 20180079848 15/562767 |
Document ID | / |
Family ID | 57005926 |
Filed Date | 2018-03-22 |
United States Patent
Application |
20180079848 |
Kind Code |
A1 |
OHNISHI; Tomofumi ; et
al. |
March 22, 2018 |
POLYMERIZABLE COMPOSITION FOR OPTICAL MEMBER, OPTICAL MEMBER, AND
SPECTACLE LENS BASE
Abstract
Provided is a polymerizable composition for an optical component
which has excellent coloring performance. [1] A polymerizable
composition for an optical component, including a urethane acrylate
represented by general formula (1), and a photochromic compound.
[2] An optical component obtained by polymerizing the polymerizable
composition. [3] A spectacle lens substrate formed from the optical
component.
Inventors: |
OHNISHI; Tomofumi; (Tokyo,
JP) ; KOUSAKA; Masahisa; (Tokyo, JP) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
HOYA LENS THAILAND LTD. |
Thanyaburi, Patumthani |
|
TH |
|
|
Assignee: |
HOYA LENS THAILAND LTD.
Thanyaburi, Patumthani
TH
|
Family ID: |
57005926 |
Appl. No.: |
15/562767 |
Filed: |
March 31, 2016 |
PCT Filed: |
March 31, 2016 |
PCT NO: |
PCT/JP2016/060731 |
371 Date: |
September 28, 2017 |
Current U.S.
Class: |
1/1 |
Current CPC
Class: |
C08K 5/357 20130101;
C08F 222/1006 20130101; G02B 1/041 20130101; C08G 18/6795 20130101;
G02C 7/102 20130101; C08G 18/7671 20130101; C08F 290/067 20130101;
C08K 5/1545 20130101; G02B 5/23 20130101; C08G 18/244 20130101;
C08K 5/3435 20130101; G02C 7/10 20130101; C08K 5/18 20130101; C08F
290/06 20130101; C08F 222/1065 20200201; C08F 222/102 20200201;
C08F 222/1065 20200201; C08F 222/1025 20200201; C08F 222/1065
20200201; C08F 222/103 20200201; C08F 222/1065 20200201; C08F
222/1025 20200201 |
International
Class: |
C08F 290/06 20060101
C08F290/06; C08K 5/357 20060101 C08K005/357; C08K 5/18 20060101
C08K005/18; C08K 5/3435 20060101 C08K005/3435; C08K 5/1545 20060101
C08K005/1545; G02B 1/04 20060101 G02B001/04; G02C 7/10 20060101
G02C007/10 |
Foreign Application Data
Date |
Code |
Application Number |
Mar 31, 2015 |
JP |
2015-072031 |
Claims
1. A polymerizable composition for an optical component, comprising
a urethane acrylate represented by general formula (1), and a
photochromic compound: ##STR00021## wherein Ar represents a residue
obtained by removing an isocyanate group from an aromatic
diisocyanate compound, R.sub.1 represents an alkanediyl group
having 2 to 4 carbon atoms, and R.sub.2 represents a hydrogen atom
or a methyl group; n represents an average number of moles added,
and is 2 to 8.
2. The polymerizable composition according to claim 1, wherein Ar
has a structure represented by general formula (a): ##STR00022##
wherein * represents a bonding site.
3. The polymerizable composition according to claim 1, wherein the
photochromic compound has a molecular weight of 800 or less.
4. The polymerizable composition according to claim 1, wherein a
content of the urethane acrylate in the composition is 60% by mass
to 99% by mass.
5. The polymerizable composition according to claim 1, wherein a
content of the photochromic compound in the composition is 0.01% by
mass to 0.1% by mass.
6. The polymerizable composition according to claim 1, further
comprising a polyfunctional (meth)acrylate.
7. The polymerizable composition according to claim 6, wherein the
polyfunctional (meth)acrylate is a (poly)alkylene glycol
di(meth)acrylate.
8. The polymerizable composition according to claim 7, wherein the
polyfunctional (meth)acrylate is a (poly)alkylene glycol
diacrylate.
9. The polymerizable composition according to claim 6, wherein a
content of the polyfunctional (meth)acrylate in the composition is
1% by mass to 40% by mass.
10. An optical component obtained by polymerizing the polymerizable
composition according to claim 1.
11. A spectacle lens substrate comprising the optical component
according to claim 10.
Description
TECHNICAL FIELD
[0001] The present disclosure relates to a polymerizable
composition for an optical component, an optical component, and a
spectacle lens substrate, and more particularly to a polymerizable
composition for an optical component including a photochromic
compound.
BACKGROUND ART
[0002] Spectacle lenses using photochromic compounds are
commercially available. Such lenses have an antiglare effect as
high-density color lenses by developing color in bright outdoors
and recover high transparency when transferred indoors.
[0003] PTL 1 describes a composition for an optical material
including one or more isocyanate compounds selected from an
aliphatic isocyanate compound and an alicyclic isocyanate compound,
a bifunctional or higher functional active hydrogen compound, and a
photochromic compound.
CITATION LIST
Patent Literature
[0004] [PTL 1] WO 2014/002844
SUMMARY
Technical Problem
[0005] In a urethane polymerizable composition, the coloring
performance of the photochromic compound is lost after curing, and
it is difficult to obtain an optical component having excellent
coloring performance.
[0006] Accordingly, in an embodiment of the present disclosure,
there is provided a polymerizable composition for an optical
component, an optical component, and a spectacle lens substrate
having excellent coloring performance.
Solution to Problem
[0007] The inventors of the present disclosure have found that by
using a specific urethane acrylate, high coloring performance of
the photochromic compound can be maintained even after curing. This
finding led to the completion of the present disclosure.
[0008] Thus, the present disclosure relates to the following [1] to
[3].
[0009] [1] A polymerizable composition for an optical component,
including a urethane acrylate represented by general formula (1),
and a photochromic compound:
##STR00001##
wherein, in the formula, Ar represents a residue obtained by
removing an isocyanate group from an aromatic diisocyanate
compound, R.sub.1 represents an alkanediyl group having 2 to 4
carbon atoms, and R.sub.2 represents a hydrogen atom or a methyl
group; n represents an average number of moles added, and is 2 to
8].
[0010] An optical component obtained by polymerizing the
polymerizable composition according to clause [1].
[0011] A spectacle lens substrate formed from the optical component
according to clause [2].
Advantageous Effects of Invention
[0012] According to the present disclosure, it is possible to
provide a polymerizable composition for an optical component, an
optical component, and a spectacle lens substrate having excellent
coloring performance.
DESCRIPTION OF EMBODIMENTS
[0013] [Polymerizable Composition for Optical Component]
[0014] The polymerizable composition for an optical component of
the present disclosure includes a urethane acrylate represented by
general formula (1), and a photochromic compound. It is conceivable
that by including the urethane acrylate represented by general
formula (1), it is possible to obtain an optical component which
has excellent coloring performance and in which structural changes
of the photochromic compound caused by light in the resin matrix
are unlikely to be inhibited even in the composition after
curing.
[0015] <Urethane Acrylate>
[0016] The urethane acrylate used in the present disclosure is
represented by the following general formula (1). By using the
urethane acrylate, it is possible to obtain an optical component
having excellent coloring performance, high toughness and high
refractive index,
##STR00002##
wherein, in the formula, Ar represents a residue obtained by
removing an isocyanate group from an aromatic diisocyanate
compound, R.sub.1 represents an alkanediyl group having 2 to 4
carbon atoms, and R.sub.2 represents a hydrogen atom or a methyl
group; n represents an average number of moles added, and is 2 to
8.
[0017] Ar is a residue obtained by removing an isocyanate group
from an aromatic diisocyanate compound in order to obtain excellent
toughness.
[0018] In order to obtain excellent toughness, Ar may have a
structure represented by the following general formula (a):
##STR00003##
wherein, in the formula, * represents a binding site.
[0019] In the above structure, the binding site * is exemplified by
a 4,4'-position and a 2,4'-position, among which the 4,4'-position
may have better.
[0020] Examples of the aromatic diisocyanate include sulfur-free
aromatic isocyanates such as 4,4'-diphenylmethane diisocyanate,
2,4'-diphenylmethane diisocyanate, paraphenylene diisocyanate,
metaphenylene diisocyanate, 2,6-tolylene diisocyanate, 2,4-tolylene
diisocyanate, paraxylylene diisocyanate, metaxylylene diisocyanate,
paratetramethylxylylene diisocyanate, metaparatetramethylxylylene
diisocyanate, 2,6-naphthalene diisocyanate, 1,5-naphthalene
diisocyanate, and the like; and sulfur-containing isocyanate
compounds such as diphenyl disulfide-4,4'-diisocyanate,
2,2'-dimethyldiphenyl disulfide-5,5'-diisocyanate,
3,3'-dimethyldiphenyl disulfide-5,5'-diisocyanate,
3,3'-dimethyldiphenyl disulfide-6,6'-diisocyanate,
4,4'-dimethyldiphenyl disulfide-5,5'-diisocyanate,
3,3'-dimethoxydiphenyl disulfide-4,4'-diisocyanate,
4,4'-dimethoxydiphenyl disulfide-3,3'-diisocyanate,
diphenylsulfone-4,4'-diisocyanate,
diphenylsulfone-3,3'-diisocyanate,
benzylidenesulfone-4,4'-diisocyanate,
diphenylmethanesulfone-4,4'-diisocyanate,
4-methyldiphenylmethanesulfone-2,4'-diisocyanate,
4,4'-dimethoxydiphenylsulfone-3,3'-diisocyanate,
3,3'-dimethoxy-4,4'-diisocyanatodibenzylsulfone,
4,4'-dimethyldiphenylsulfone-3,3'-diisocyanate,
4,4'-di-tert-butyldiphenylsulfone-3,3'-diisocyanate,
4,4'-dimethoxybenzene-ethylenedisulfone-3,3'-diisocyanate,
4,4'-dichlorodiphenylsulfone-3,3'-diisocyanate,
4-methyl-3-isocyanatobenzenesulfonyl-4'-isocyanatophenol ester,
4-methoxy-3-isocyanatobenzenesulfonyl-4'-isocyanatophenol ester,
4-methyl-3-isocyanatobenzenesulfonylanilide-3'-methyl-4'-isocyanate,
dibenzenesulfonyl-ethylenediamine-4,4'-diisocyanate,
4,4'-dimethoxybenzenesulfonyl-ethylenediamine-3,3'-diisocyanate,
4-methyl-3-isocyanatobenzenesulfonylanilide-4-methyl-3'-isocyanate,
thiophene-2,5-diisocyanate, thiophene-2,5-diisocyanatomethyl and
the like.
[0021] Among them, at least one of 4,4'-diphenylmethane
diisocyanate, 2,4'-diphenylmethane diisocyanate, 2,6-tolylene
diisocyanate, 2,4-tolylene diisocyanate, paraxylylene diisocyanate,
and metaxylylene diisocyanate may have better, 4,4'-diphenylmethane
diisocyanate may have better.
[0022] R.sub.1 may be an alkanediyl group having 2 or 3 carbon
atoms, and an ethanediyl group.
[0023] R.sup.2 may be a methyl group.
[0024] n represents an average number of moles added; from the
viewpoint of maintaining excellent light control of the
photochromic compound after curing of the composition, this number
is 2 to 8, and may be 3 to 6, and 4 to 6.
[0025] The urethane acrylate may be a compound represented by the
following general formula (11):
##STR00004##
wherein, in the formula, n represents an average number of moles
added and is 2 to 8, may be 3 to 6, and 4 to 6.
[0026] The urethane acrylate may be obtained, for example, by
reacting an aromatic diisocyanate and a polyalkylene glycol
acrylate in an amount equivalent to that of the isocyanate group in
the aromatic diisocyanate. For the reaction, an organotin compound
such as dimethyltin dichloride may be used as a polymerization
catalyst. The reaction may be carried out at a temperature of
25.degree. C. to 80.degree. C. under a nitrogen atmosphere.
[0027] The content of the urethane acrylate in the composition may
be 60% by mass or more, 70% by mass or more, 72% by mass or more,
75% by mass or more, and 80% by mass or more. The content in the
composition may be 99% by mass or less, 95% by mass or less, 89% by
mass or less, and 87% by mass or less.
[0028] <Other Polyfunctional (Meth)Acrylate>
[0029] The polymerizable composition for an optical component of
the present disclosure may contain another polyfunctional
(meth)acrylate to improve a fading rate.
[0030] The polyfunctional (meth)acrylate is exemplified by a
compound represented by the following general formula (2):
##STR00005##
wherein, in the formula, R.sub.21 represents an alkanediyl group
having 2 to 4 carbon atoms; R.sub.22 represents a hydrogen atom or
a methyl group; R.sub.25 represents a residue obtained by removing
a hydrogen atom of one hydroxy group and k hydroxy groups from a
(k+1)-hydric or higher alcohol; j is 0 or 1, k is an integer of 1
to 3, and m and n each represent an average number of moles added,
and is 0 to 30. However, when j is 0, k is 1 and n is 0.
[0031] R.sub.21 may be an alkanediyl group having 2 or 3 carbon
atoms, and an ethanediyl group.
[0032] From the viewpoint of reducing the fading time, R.sub.22 may
be a hydrogen atom.
[0033] The (k+1)-hydric or higher alcohol of R.sub.25 (also
referred to hereinbelow as "polyhydric alcohol") may be exemplified
by bisphenol A [2,2-bis(4,4'-dihydroxyphenyl)propane],
trimethylolpropane, pentaerythritol, dipentaerythritol and the
like.
[0034] k may be 1.
[0035] m and n each represent an average number of moles added, and
may be from 2 to 25, from 3 to 15, from 4 to 10, and from 4 to 6,
from the viewpoint of obtaining excellent coloring performance of
the photochromic compound after curing of the composition.
[0036] The polyfunctional (meth)acrylate may be exemplified by
(poly)alkylene glycol di(meth)acrylates, ethoxylated bisphenol A
dimethacrylate, and trimethylolpropane trimethacrylate.
[0037] From the viewpoint of improving the fading rate, the content
of the polyfunctional (meth)acrylate in the composition may be 1%
by mass or more, 5% by mass or more, 11% by mass or more, and 13%
by mass or more. The content in the composition may be 40 mass % or
less, 30 mass % or less, 28 mass % or less, 25 mass % or less, and
20 mass % or less.
[0038] Among these polyfunctional (meth)acrylates, a (poly)alkylene
glycol di(meth)acrylate may have better.
[0039] [(Poly)Alkylene Glycol Di(Meth)Acrylate]
[0040] The polymerizable composition for an optical component of
the present disclosure may include a (poly)alkylene glycol
di(meth)acrylate.
[0041] (Poly)alkylene glycol means at least one selected from a
polyalkylene glycol and an alkylene glycol.
[0042] (Meth)acrylate means at least one selected from acrylate and
methacrylate.
[0043] A (poly)alkylene glycol di(meth)acrylate may be a compound
represented by the following general formula (2-1):
##STR00006##
wherein, in the formula, R.sub.21 represents an alkanediyl group
having 2 to 4 carbon atoms, and R.sub.22 represents a hydrogen atom
or a methyl group; m represents the average number of moles added,
and is 2 to 30.
[0044] Examples of R.sub.21 are the same as those in general
formula (2).
[0045] Examples of R.sub.22 are the same as those in general
formula (2).
[0046] m represents the average number of moles added. From the
viewpoint of maintaining the excellent light control property of
the photochromic compound after curing of the composition, this
number may be from 2 to 25, from 3 to 15, from 4 to 10, and from 4
to 6.
[0047] From the viewpoint of improving the coloring performance and
shortening the fading time, the (poly)alkylene glycol
di(meth)acrylate may be a (poly)alkylene glycol diacrylate, and
polyethylene glycol diacrylate.
[0048] Commercial products of polyethylene glycol diacrylate are
exemplified by trade names A-200, A-400, A-600, and A-1000
manufactured by Shin-Nakamura Chemical Co., Ltd.
[0049] The content of the (poly)alkylene glycol di(meth)acrylate in
the composition may be 1% by mass or more, 5% by mass or more, and
may be from the viewpoint of further shortening the fading time,
11% by mass or more, and 13 mass % or more. The content may be 30
mass % or less, 28 mass % or less, 25 mass % or less, and 20 mass %
or less.
[0050] <Other Acrylate>
[0051] The polymerizable composition for an optical component of
the present disclosure may include another acrylate. Examples of
the other acrylate include an alkyl methacrylate with an alkyl
group having 1 to 4 carbon atoms, benzyl methacrylate, allyl
phthalate and the like.
[0052] <Photochromic Compound>
[0053] Examples of the photochromic compound include fulgimide
compounds, spirooxazine compounds, chromene compounds and the
like.
[0054] The molecular weight of the photochromic compound may be 800
or less, 780 or less, 750 or less, in order to improve the coloring
density and the fading rate. The molecular weight may be 300 or
more, 400 or more, and 500 or more.
[0055] Well-known compounds may be used as the fulgimide compounds,
spirooxazine compounds, and chromene compounds.
[0056] Among these photochromic compounds, the chromene
photochromic compounds may have better because the durability of
the photochromic property is higher than that of other photochromic
compounds and the improvement of coloring density and fading rate
of the photochromic property is particularly large as compared with
other photochromic compounds.
[0057] Further, as the chromene photochromic compound having
particularly good photochromic properties such as coloring density,
color fading rate, durability and the like, those represented by
the following general formula (3) may have better,
##STR00007##
wherein, in the formula, a group represented by general formula
(3a):
##STR00008##
is a substituted or unsubstituted aromatic hydrocarbon group or a
substituted or unsubstituted unsaturated heterocyclic group,
R.sup.43, R.sup.44 and R.sup.45 are each independently a hydrogen
atom, an alkyl group, an alkoxy group, an aralkoxy group, an amino
group, a substituted amino group, a cyano group, a substituted or
unsubstituted aryl group, a halogen atom, an aralkyl group, a
hydroxyl group, a substituted or unsubstituted alkynyl group, a
substituted or unsubstituted heterocyclic group which has a
nitrogen atom and in which the nitrogen atom is bonded to a pyran
ring or a ring of the group represented by formula (3a), or a
condensed heterocyclic group in which an aromatic hydrocarbon ring
or an aromatic heterocyclic ring is condensed on the heteroatom
ring, and c is an integer within a range from 0 to 6,
[0058] R.sup.41 and R.sup.42 are each independently a substituted
or unsubstituted alkenyl group, a substituted or unsubstituted
alkynyl group, a substituted or unsubstituted aryl group, a
substituted or unsubstituted heteroaryl group, or an alkyl group,
or R.sup.41 and R.sup.42 may form a substituted or unsubstituted
aliphatic hydrocarbon ring or aromatic hydrocarbon ring.
[0059] Examples of the substituent in the substituted aryl group
and substituted heteroaryl group described for R.sup.41 and
R.sup.42 include the same groups as those relating to R.sup.43 to
R.sup.44
[0060] Among the chromene photochromic compounds represented by
general formula (3), those represented by the following general
formulas (31) to (36) may have better from the viewpoints of
photochromic properties such as coloring density and fading rate
and durability,
##STR00009##
wherein, in the formula, R.sup.49 and R.sup.50 are the same as
R.sup.41 and R.sup.42, respectively, of general formula (3),
R.sup.51 and R.sup.52 are the same as R.sup.45 of general formula
(3), q and q' are each 1 or 2,
##STR00010##
wherein, in the formula, R.sup.53 and R.sup.54 are the same as
R.sup.4 and R.sup.42 respectively, of general formula (3), R.sup.55
and R.sup.56 are the same as R.sup.45 of general formula (3), L is
any group represented by the following formulas:
##STR00011##
wherein, in the formulas, P is an oxygen atom or a sulfur atom,
R.sup.57 is an alkylene group having 1 to 6 carbon atoms, s, s' and
s'' are each an integer of 1 to 4), and r and r' are each
independently 1 or 2,
##STR00012##
wherein, in the formula, R.sup.58 and R.sup.59 are the same as
R.sup.41 and R.sup.42, respectively, of general formula (3),
R.sup.60, R.sup.61 and R.sup.62 are the same as R.sup.45 of general
formula (3), v is 1 or 2,
##STR00013##
wherein, in the formula, R.sup.63 and R.sup.64 are the same as
R.sup.41 and R.sup.42, respectively, of general formula (3),
R.sup.65 and R.sup.66 are the same as R.sup.45 of general formula
(3), w and w' are each independently 1 or 2,
##STR00014##
wherein, in the formula, R.sup.67 and R.sup.68 are the same as
R.sup.41 and R.sup.42, respectively, of general formula (3),
R.sup.69, R.sup.70, R.sup.71 and R.sup.72 are each the same as
R.sup.45 of general formula (3), and x and x' are each
independently 1 or 2,
##STR00015##
Wherein, in the formula, R.sup.73 and R.sup.74 are the same as
R.sup.41 and R.sup.42, respectively, of general formula (3), and
R.sup.75, R.sup.76 and R.sup.77 are the same as R.sup.45 of general
formula (3),
##STR00016##
is an aliphatic hydrocarbon ring which may have at least one
substituent, and each of y, y' and y'' is independently 1 or 2.
[0061] Among the chromene photochromic compounds represented by
general formulas (31) to (36), chromene compounds (compounds 3-1 to
3-6) having the following structures may have better.
##STR00017## ##STR00018##
[0062] These photochromic compounds may be used by appropriately
mixing a plurality of types the compounds in order to develop an
appropriate color tone.
[0063] From the viewpoint of further reducing the fading time, the
content of the photochromic compound in the composition may be
0.01% by mass or more, 0.03% by mass or more, and 0.05% by mass or
more. The content may be 1% by mass or less, 0.5% by mass or less,
and 0.1% by mass or less.
[0064] The polymerizable composition for an optical component may
further include an additive such as a surfactant, an antioxidant, a
radical scavenger, an ultraviolet stabilizer, an ultraviolet
absorber, a release agent, a coloring inhibitor, an antistatic
agent, a fluorescent dye, a dye, a pigment, a perfume, a
plasticizer and the like. As these additives, known compounds may
be used without any limitation.
[0065] [Method for Producing Optical Component]
[0066] A method for producing an optical component may include a
step of curing the polymerizable composition for an optical
component.
[0067] The step of curing may be carried out by casting the
polymerizable composition into a mold obtained by assembling a
glass mold or a metal mold and a resin gasket or a tape, and
polymerizing the monomer by heating or ultraviolet irradiation or
the like.
[0068] In the curing step, a radical initiator may be used.
Examples of the radical initiator include
2,2'-azobis(2,4-dimethylvaleronitrile), 1,1-azobiscyclohexane
carbonate, diisopropyl peroxycarbonate, 1,1'-azobiscyclohexane
nitrate, di-tert-butyl peroxide and the like.
[0069] The compounded amount of the radical initiator may be 0.1
part by mass or more and 10 percent by mass or less with respect to
100 parts by mass of the polymerizable composition for an optical
component.
[0070] [Optical Component]
[0071] The optical component of the present disclosure may be a
lens substrate or a functional layer, may be a lens substrate, and
a spectacle lens substrate.
[0072] The functional layer may be exemplified by at least one
selected from a hard coat layer, a primer layer, an antireflection
film, and a water repellent film.
[0073] The hard coat layer is provided for improving scratch
resistance and may be formed by coating a coating liquid having a
fine particulate inorganic material such as an organosilicon
compound, tin oxide, silicon oxide, zirconium oxide, titanium
oxide, and the like.
[0074] The primer layer is provided for improving impact resistance
and includes, for example, polyurethane as a main component. Here,
the polyurethane content in the primer layer may be 50% by mass or
more.
[0075] The antireflection film may be exemplified by a film
obtained by laminating silicon oxide, titanium dioxide, zirconium
oxide, tantalum oxide or the like.
[0076] The water repellent film may be formed using an
organosilicon compound having a fluorine atom.
[0077] When the plastic optical component of the present disclosure
is used for a lens substrate, the refractive index of the lens
substrate may be 1.49 or more, and 1.54 or more. The refractive
index may be 1.78 or less, 1.75 or less, 1.68 or less, 1.61 or
less, and 1.57 or less.
[0078] In the present disclosure, matters described as examples or
preferred ranges in the detailed description of the disclosure may
be arbitrarily combined with respect to the examples, contents, and
physical properties of each of the above-mentioned components.
[0079] Further, where the composition described in the detailed
description of the disclosure is adjusted to the composition
described in the examples, the disclosed embodiments can be carried
out in the same manner as in the examples over the entire
composition range claimed.
EXAMPLES
[0080] The present disclosure will be specifically described
hereinbelow by way of examples, but the present disclosure is not
limited to these examples. Various physical properties were
measured and evaluated by the following methods.
[0081] [Light Control Performance Test]
[0082] <Method for Evaluating Light Control Performance>
[0083] (a) Light transmittance at the time of color development (T
%.sub.max): a lens was subjected to color development for 5 min by
using a xenon lamp (300 W) light source device under the conditions
of a temperature of 23.degree. C. and an ultraviolet intensity of
1.2 mW/cm.sup.2 measured with an integrated photometer, and a
spectrum at this time was measured by the instantaneous
multi-photometry system. Concerning the measured spectrum, the
light transmittance at the maximum absorption wavelength
(.lamda..sub.max) is defined as the light transmittance at the time
of color development (T %.sub.max). The lower is the light
transmittance, the higher is the color density.
[0084] (b) 60% T fading time (F1/2): this time is defined as a time
required for the absorbance at the maximum absorption wavelength
(.lamda..sub.max) to decrease to 60% T after the irradiation with
light is stopped following the aforementioned color development for
5 min. The shorter is this time, the higher is the fading rate.
[0085] <Apparatus Used>
[0086] Light source device: a xenon lamp (300 W) device "UIT-501C",
manufactured by Ushio Inc.
[0087] Integrated photometer: integrated photometer "UIT-102
(Receiver UVD365PD)", manufactured by Ushio Inc.
[0088] Instantaneous multi-photometry system: "MCPD-3000",
manufactured by Otsuka Electronics Co., Ltd.
[0089] [Tensile Strength Test]
[0090] A flat plate having a diameter of 50 mm and a plate
thickness of 1.8 mm was prepared and two 2.0 mm holes were opened
at two locations horizontally at 1800 with respect to each other at
2 mm from the end portion. Then, SUS rods were passed through the
holes, a tensile load was applied at a rate of 5 mm/min by using a
Tensilon universal testing machine RTC-1225, and the breakdown load
and elongation at break were measured.
Production Example 1 [Production Method of Compound 1-1]
[0091] A total of 0.01 g of dimethyltin dichloride as a
polymerization catalyst was added to 30.6 g of 4,4'-diphenylmethane
diisocyanate, which is a polyisocyanate compound having an aromatic
ring, in a 300 ml eggplant-shaped flask, and dissolution was
performed under a nitrogen atmosphere at 50.degree. C. with a
stirrer for 30 min.
[0092] Next, 69.4 g of polyoxyethylene monomethacrylate (trade
name: BLEMMER PE-200, manufactured by NOF Corporation) was
compounded as a polyol compound and stirring was performed for 60
min at 50.degree. C. under a nitrogen atmosphere to obtain Compound
1-1.
Example 1
[0093] A total of 84 g of Compound 1-1, 16 g of polyethylene glycol
diacrylate (trade name: NK ESTER A-200, manufactured by
Shin-Nakamura Chemical Co., Ltd., average number of moles added of
ethylene glycol: 4), 0.1 g of 2,2'-azobis
(2,4-dimethylvaleronitrile) (trade name: V-65 manufactured by Wako
Pure Chemical Industries, Ltd.) as a radical initiator, 0.07 g of
the above-described Compound 3-1 as a photochromic compound, and
0.15 g of a mixture of butoxyethyl acid phosphate and dibutoxyethyl
acid phosphate (mass ratio 5:5) as a release agent were placed into
a 300 mL eggplant-shaped flask and dissolution was performed under
stirring. Then, stirring was performed for 30 min under reduced
pressure at 0.5 kPa to prepare a composition. This composition was
filtered using a 1.0 .mu.m polytetrafluoroethylene (referred to
hereinbelow as "PTFE").cndot.membrane filter. The filtrate was
poured into a mold made of a glass mold and a tape. Casting
polymerization was carried out for 24 h at a temperature program
from 40.degree. C. to a final temperature of 100.degree. C. to
obtain a spectacle lens substrate having a thickness of 2.0 mm. The
spectacle lens substrate was further annealed for 2 h at
100.degree. C.
Example 2
[0094] A total of 84 g of Compound 1-1, 16 g of ethoxylated
bisphenol A dimethacrylate (trade name: BPE-500, manufactured by
Shin-Nakamura Chemical Co., Ltd., average number of moles added of
ethylene glycol: 10 (calculated for both ends)), 0.1 g of
2,2'-azobis (2,4-dimethylvaleronitrile) (trade name: V-65
manufactured by Wako Pure Chemical Industries, Ltd.) as a radical
initiator, 0.07 g of the above-described Compound 3-1 as a
photochromic compound, and 0.15 g of a mixture of butoxyethyl acid
phosphate and dibutoxyethyl acid phosphate (mass ratio 5:5) as a
release agent were placed into a 300 mL eggplant-shaped flask and
dissolution was performed under stirring. Then, stirring was
performed for 30 min under reduced pressure at 0.5 kPa to prepare a
composition. This composition was filtered using a 1.0 .mu.m
PTFE.cndot.membrane filter. The filtrate was poured into a mold
made of a glass mold and a tape. Casting polymerization was carried
out for 24 h at a temperature program from 40.degree. C. to a final
temperature of 100.degree. C. to obtain a spectacle lens substrate
having a thickness of 2.0 mm. The spectacle lens substrate was
further annealed for 2 h at 100.degree. C.
Example 3
[0095] A total of 84 g of Compound 1-1, 16 g of polyethylene glycol
dimethacrylate (trade name: NK ESTER 4G, manufactured by
Shin-Nakamura Chemical Co., Ltd., average number of moles added of
ethylene glycol: 4), 0.1 g of 2,2'-azobis
(2,4-dimethylvaleronitrile) (trade name: V-65 manufactured by Wako
Pure Chemical Industries, Ltd.) as a radical initiator, 0.07 g of
the above-described Compound 3-1 as a photochromic compound, and
0.15 g of a mixture of butoxyethyl acid phosphate and dibutoxyethyl
acid phosphate (mass ratio 5:5) as a release agent were placed into
a 300 mL eggplant-shaped flask and dissolution was performed under
stirring. Then, stirring was performed for 30 min under reduced
pressure at 0.5 kPa to prepare a composition. This composition was
filtered using a 1.0 .mu.m PTFE.cndot.membrane filter. The filtrate
was poured into a mold made of a glass mold and a tape. Casting
polymerization was carried out for 24 h at a temperature program
from 40.degree. C. to a final temperature of 100.degree. C. to
obtain a spectacle lens substrate having a thickness of 2.0 mm. The
spectacle lens substrate was further annealed for 2 h at
100.degree. C.
Example 4
[0096] A total of 84 g of Compound 1-1, 16 g of trimethylolpropane
trimethacrylate (trade name: NK ESTER TMPT, manufactured by
Shin-Nakamura Chemical Co., Ltd.), 0.1 g of 2,2'-azobis
(2,4-dimethylvaleronitrile) (trade name: V-65 manufactured by Wako
Pure Chemical Industries, Ltd.) as a radical initiator, 0.07 g of
the above-described Compound 3-1 as a photochromic compound, and
0.15 g of a mixture of butoxyethyl acid phosphate and dibutoxyethyl
acid phosphate (mass ratio 5:5) as a release agent were placed into
a 300 mL eggplant-shaped flask and dissolution was performed under
stirring. Then, stirring was performed for 30 min under reduced
pressure at 0.5 kPa to prepare a composition. This composition was
filtered using a 1.0 .mu.m PTFE.cndot.membrane filter. The filtrate
was poured into a mold made of a glass mold and a tape. Casting
polymerization was carried out for 24 h at a temperature program
from 40.degree. C. to a final temperature of 100.degree. C. to
obtain a spectacle lens substrate having a thickness of 2.0 mm. The
spectacle lens substrate was further annealed for 2 h at
100.degree. C.
Example 5
[0097] A total of 90 g of Compound 1-1, 10 g of polyethylene glycol
diacrylate (trade name: NK ESTER A-200, manufactured by
Shin-Nakamura Chemical Co., Ltd.), 0.1 g of 2,2'-azobis
(2,4-dimethylvaleronitrile) (trade name: V-65 manufactured by Wako
Pure Chemical Industries, Ltd.) as a radical initiator, 0.07 g of
the above-described Compound 3-1 as a photochromic compound, and
0.15 g of a mixture of butoxyethyl acid phosphate and dibutoxyethyl
acid phosphate (mass ratio 5:5) as a release agent were placed into
a 300 mL eggplant-shaped flask and dissolution was performed under
stirring. Then, stirring was performed for 30 min under reduced
pressure at 0.5 kPa to prepare a composition. This composition was
filtered using a 1.0 .mu.m PTFE.cndot.membrane filter. The filtrate
was poured into a mold made of a glass mold and a tape. Casting
polymerization was carried out for 24 h at a temperature program
from 40.degree. C. to a final temperature of 100.degree. C. to
obtain a spectacle lens substrate having a thickness of 2.0 mm. The
spectacle lens substrate was further annealed for 2 h at
100.degree. C.
Example 6
[0098] A total of 94 g of Compound 1-1, 6 g of polyethylene glycol
diacrylate (trade name: NK ESTER A-200, manufactured by
Shin-Nakamura Chemical Co., Ltd.), 0.1 g of 2,2'-azobis
(2,4-dimethylvaleronitrile) (trade name: V-65 manufactured by Wako
Pure Chemical Industries, Ltd.) as a radical initiator, 0.07 g of
the above-described Compound 3-1 as a photochromic compound, and
0.15 g of a mixture of butoxyethyl acid phosphate and dibutoxyethyl
acid phosphate (mass ratio 5:5) as a release agent were placed into
a 300 mL eggplant-shaped flask and dissolution was performed under
stirring. Then, stirring was performed for 30 min under reduced
pressure at 0.5 kPa to prepare a composition. This composition was
filtered using a 1.0 .mu.m PTFE.cndot.membrane filter. The filtrate
was poured into a mold made of a glass mold and a tape. Casting
polymerization was carried out for 24 h at a temperature program
from 40.degree. C. to a final temperature of 100.degree. C. to
obtain a spectacle lens substrate having a thickness of 2.0 mm. The
spectacle lens substrate was further annealed for 2 h at
100.degree. C.
Example 7
[0099] A total of 97 g of Compound 1-1, 3 g of polyethylene glycol
diacrylate (trade name: NK ESTER A-200, manufactured by
Shin-Nakamura Chemical Co., Ltd.), 0.1 g of 2,2'-azobis
(2,4-dimethylvaleronitrile) (trade name: V-65 manufactured by Wako
Pure Chemical Industries, Ltd.) as a radical initiator, 0.07 g of
the above-described Compound 3-1 as a photochromic compound, and
0.15 g of a mixture of butoxyethyl acid phosphate and dibutoxyethyl
acid phosphate (mass ratio 5:5) as a release agent were placed into
a 300 mL eggplant-shaped flask and dissolution was performed under
stirring. Then, stirring was performed for 30 min under reduced
pressure at 0.5 kPa to prepare a composition. This composition was
filtered using a 1.0 .mu.m PTFE.cndot.membrane filter. The filtrate
was poured into a mold made of a glass mold and a tape. Casting
polymerization was carried out for 24 h at a temperature program
from 40.degree. C. to a final temperature of 100.degree. C. to
obtain a spectacle lens substrate having a thickness of 2.0 mm. The
spectacle lens substrate was further annealed for 2 h at
100.degree. C.
Reference Example 1: Acrylic Spectacle Lens Substrate
[0100] A total of 80 g of ethoxylated bisphenol A dimethacrylate
(trade name: BPE-100, manufactured by Shin-Nakamura Chemical Co.,
Ltd.), 20 g of ethoxylated bisphenol A dimethacrylate (trade name:
BPE-500, manufactured by Shin-Nakamura Chemical Co., Ltd.), 0.1 g
of 2,2'-azobis (2,4-dimethylvaleronitrile) (trade name: V-65
manufactured by Wako Pure Chemical Industries, Ltd.) as a radical
initiator, 0.07 g of the above-described Compound 3-1 as a
photochromic compound, and 0.001 g of modified silicone oil (trade
name: KF-353A, manufactured by Shin-Etsu Chemical Co., Ltd.) as a
release agent were placed into a 300 mL eggplant-shaped flask and
dissolution was performed under stirring. Then, stirring was
performed for 30 min under reduced pressure at 0.5 kPa to prepare a
composition. This composition was filtered using a 1.0 .mu.m
PTFE.cndot.membrane filter. The filtrate was poured into a mold
made of a glass mold and a tape. Casting polymerization was carried
out for 24 h at a temperature program from 40.degree. C. to a final
temperature of 100.degree. C. to obtain a spectacle lens substrate
having a thickness of 2.0 mm. The spectacle lens substrate was
further annealed for 2 h at 100.degree. C.
Comparative Example 1: Urethane Spectacle Lens Substrate
[0101] A total of 50 g of 2,5(2,6)-bis(isocyanatomethyl)bicyclo
heptane (trade name: MR-8A solution, manufactured by Mitsui
Chemicals, Inc.), 0.01 g of dimethyltin dichloride as a radical
initiator, and 0.07 g of the above-described Compound 3-1 as a
photochromic compound were placed into a 300 mL eggplant-shaped
flask, 0.15 g of a mixture of butoxyethyl acid phosphate and
dibutoxyethyl acid phosphate (mass ratio 5:5) was added as a
release agent, and dissolution was performed under stirring for 10
min at 15.degree. C. by using a stirrer. Then, 25 g of MR-8B1
(trade name: MR-8B1 solution, manufactured by Mitsui Chemicals,
Inc.) and 25 g of MR-8B2 (trade name: MR-8B2 solution, manufactured
by Mitsui Chemicals, Inc.) were added as polythiol compounds,
followed by stirring. Then, stirring was performed for 30 min under
reduced pressure at 0.5 kPa to prepare a composition. This
composition was filtered using a 1.0 .mu.m PTFE.cndot.membrane
filter. The filtrate was poured into a mold made of a glass mold
and a tape. Casting polymerization was carried out for 24 h at a
temperature program from 20.degree. C. to a final temperature of
120.degree. C. to obtain a spectacle lens substrate having a
thickness of 2.0 mm. The spectacle lens substrate was further
annealed for 2 h at 120.degree. C.
TABLE-US-00001 TABLE 1 Exam- Exam- Exam- Exam- ple 1 ple 2 ple 3
ple 4 Composition Compound 1-1 84 84 84 84 (g) A-200 16 BPE-500 16
4G 16 TMPT 16 Photochromic 0.07 0.07 0.07 0.07 compound 3-1 Light
transmittance at the time of 16.0% 17.8% 26.4% 23.8% color
development (T %.sub.max) 60% T fading time (sec) 280 900 900
810
TABLE-US-00002 TABLE 2 Exam- Exam- Exam- Exam- ple 1 ple 5 ple 6
ple 7 Composition Compound 1-1 84 90 94 97 (g) A-200 16 10 6 3
Photochromic 0.07 0.07 0.07 0.07 compound 3-1 Light transmittance
at the time of 16.0% 15.8% 16.1% 20.3% color development (T
%.sub.max) 60% T fading time (sec) 280 900 900 900 Tensile
Breakdown 23.9 19.6 24.5 24.3 load (kgf) test Elongation at 1.86
2.48 2.40 2.17 break (mm)
TABLE-US-00003 TABLE 3 Reference Comparative Example 1 Example 2
Composition BPE100 80 (g) BPE500 20 MR-8A 50 MR-8B1 25 MR-8B2 25
Photochromic compound 3-1 0.07 0.07 Light transmittance at the time
of color 19.0% No coloring development (T %.sub.max) or fading 60%
T fading time (sec) 390 No coloring or fading Tensile Breakdown
load (kgf) 15.0 51.2 test Elongation at break (mm) 0.80 2.02
[0102] Various components shown in the tables are described in
details hereinbelow.
[0103] Compound 1-1: The Following Compound 1-1:
##STR00019##
A-200: polyethylene glycol diacrylate (trade name: A-200,
manufactured by Shin-Nakamura Chemical Co., Ltd., average number of
moles added of ethylene glycol: 4); BPE-500: ethoxylated bisphenol
A dimethacrylate (trade name: BPE-500, manufactured by
Shin-Nakamura Chemical Co., Ltd., average number of moles added of
ethylene glycol: 10 (total for both ends)); 4G: polyethylene glycol
dimethacrylate (trade name: NK Ester 4G, manufactured by
Shin-Nakamura Chemical Co., Ltd., average number of moles added of
ethylene glycol: 4); TMPT: trimethylolpropane trimethacrylate
(trade name: NK Ester TMPT, manufactured by Shin-Nakamura Chemical
Co., Ltd.); Photochromic Compound 3-1: chromene compound which is
Compound 3-1 (molecular weight: 741.87); BPE-100: ethoxylated
bisphenol A dimethacrylate (trade name: NK Ester BPE-100,
manufactured by Shin-Nakamura Chemical Co., Ltd.); MR-8A:
2,5(2,6)-bis(isocyanatomethyl)bicyclo [2.2.1] heptane (trade name:
MR-8A solution, manufactured by Mitsui Chemicals, Inc.); MR-8B1:
polythiol (trade name: MR-8B1 solution, manufactured by Mitsui
Chemicals, Inc.); MR-8B2: polythiol (trade name: MR-8B 2 solution,
manufactured by Mitsui Chemicals, Inc.).
[0104] According to the results shown in Table 1 and the results of
Comparative Example 1 shown in Table 3, it can be understood that
excellent coloring performance is exhibited as a result of using
the urethane acrylate according to the present disclosure. Further,
according to the results shown in Table 2 and the results of
Reference Example 1 shown in Table 3, it can be understood that
excellent toughness superior to that of the conventional acrylic
spectacle lens substrates is obtained as a result of using the
urethane acrylate according to the present disclosure.
[0105] Finally, the embodiments of the present disclosure are
summarized.
[0106] One embodiment of the present disclosure is
[0107] a polymerizable composition for an optical component,
including a urethane acrylate represented by general formula (1),
and a photochromic compound:
##STR00020##
wherein, in the formula, Ar represents a residue obtained by
removing an isocyanate group from an aromatic diisocyanate
compound, R.sub.1 represents an alkanediyl group having 2 to 4
carbon atoms, and R.sub.2 represents a hydrogen atom or a methyl
group; n represents an average number of moles added, and is 2 to
8.
[0108] It is conceivable that by including the urethane acrylate
represented by general formula (1), it is possible to obtain an
optical component which has excellent coloring performance and in
which structural changes of the photochromic compound caused by
light in the resin matrix are unlikely to be inhibited even in the
composition after curing.
[0109] It should be noted that the embodiment disclosed herein is
merely exemplary in all aspects and is not intended to be
restrictive. The scope of the present disclosure is defined by the
claims, rather than by the description, and is intended to be
inclusive of meanings equivalent to the claims and all changes
within the scope thereof.
* * * * *